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G013

Sigma-Aldrich

R(+)-Baclofen hydrochloride

solid

Sinónimos:

Arbaclofen hydrochloride, R(+)-β-(Aminomethyl)-4-chlorobenzenepropanoic acid hydrochloride, STX209

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About This Item

Fórmula empírica (notación de Hill):
C10H12ClNO2 · HCl
Número de CAS:
63701-55-3
Peso molecular:
250.12
MDL number:
MFCD00078579
UNSPSC Code:
12352200
PubChem Substance ID:
24895006
NACRES:
NA.32

form

solid

Quality Level

100

optical activity

[α]28/D +3.8°, c = 0.9 in methanol(lit.)

storage condition

desiccated

color

white

solubility

DMSO: >20 mg/mL
H2O: 26 mg/mL (Solutions may be stored for several weeks at 4 °C.)

SMILES string

Cl[H].NC[C@H](CC(O)=O)c1ccc(Cl)cc1

InChI

1S/C10H12ClNO2.ClH/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14;/h1-4,8H,5-6,12H2,(H,13,14);1H/t8-;/m0./s1

InChI key

WMNUVYYLMCMHLU-QRPNPIFTSA-N

Gene Information

human ... GABBR1(2550)
mouse ... GABBR1(54393)
rat ... GABBR1(81657)

Application

R(+)-Baclofen hydrochloride has been used as a GABAB receptor agonist to study its effects on M43068-induced antinociception in rat models. It has also been used as a GABAB receptor agonist to study its effects on amphetamine-induced behavior and neurochemical responses in rat striatum.

Biochem/physiol Actions

Baclofen is a derivative of γ-aminobutyric acid (GABA) and acts as a 4-aminobutanoic acid receptor (GABAB) agonist. It interacts stereospecifically with the GABA receptor and exhibits antispastic effects.Baclofen shows therapeutic effects against paroxysmal pain of trigeminal neuralgia and spinal spasticity. R(+)-Baclofen is a more active enantiomer.

Other Notes

Same enantiomer as R(−)-baclofen free base.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Yuriko Watanabe et al.
European journal of pharmacology, 837, 88-95 (2018-08-08)
The nucleus accumbens contains delta-opioid receptors that may decrease inhibitory neurotransmission. As GABAB receptors inhibit dopamine release, decrease in activation of GABAB receptors may be a mediator of delta-opioid receptor-induced accumbal dopamine efflux. If so, accumbal dopamine efflux induced by
Intracerebral Baclofen Administration Decreases Amphetamine-Induced Behavior and Neuropeptide Gene Expression in the Striatum
Wenxia Z, et al.
Neuropsychopharmacology, 880?890-880?890 (2004)
An efficient synthesis of (R)-and (S)-baclofen via desymmetrization
Ji L, et al.
Tetrahedron Letters, 50(45), 6166-6168 (2009)
Synthesis of both enantiomers of baclofen using (R)-and (S)-N-phenylpantolactam as chiral auxiliaries
Camps P, et al.
Tetrahedron Asymmetry, 15(13) (2004)
Xia Li et al.
Neuropharmacology, 97, 357-364 (2015-05-24)
GABAB (γ-aminobutyric acid B) receptors may be a therapeutic target for anxiety disorders. Here we characterized the effects of the GABAB receptor positive allosteric modulator (PAM) BHF177 on conditioned and unconditioned physiological responses to threat in the light-enhanced startle (LES)
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